ZA200503224B - 8-Substituted imidazopyridines. - Google Patents
8-Substituted imidazopyridines. Download PDFInfo
- Publication number
- ZA200503224B ZA200503224B ZA200503224A ZA200503224A ZA200503224B ZA 200503224 B ZA200503224 B ZA 200503224B ZA 200503224 A ZA200503224 A ZA 200503224A ZA 200503224 A ZA200503224 A ZA 200503224A ZA 200503224 B ZA200503224 B ZA 200503224B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkoxy
- alkyl
- hydrogen
- hydroxy
- group
- Prior art date
Links
- 150000005232 imidazopyridines Chemical class 0.000 title description 4
- 239000001257 hydrogen Substances 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 128
- 150000002431 hydrogen Chemical group 0.000 claims description 87
- -1 1-4C-alkyl Chemical group 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 12
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 241001553014 Myrsine salicina Species 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012317 TBTU Substances 0.000 description 5
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- UKGCFMYYDATGNN-UHFFFAOYSA-N 6,6a-dihydro-1ah-indeno[1,2-b]oxirene Chemical compound C12=CC=CC=C2CC2C1O2 UKGCFMYYDATGNN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- UYJYWBMSSPHQCO-UHFFFAOYSA-N 6-(methoxymethyl)-2,3-dimethyl-8-phenylmethoxyimidazo[1,2-a]pyridine Chemical compound C12=NC(C)=C(C)N2C=C(COC)C=C1OCC1=CC=CC=C1 UYJYWBMSSPHQCO-UHFFFAOYSA-N 0.000 description 2
- ICBCHJDVBWROGM-UHFFFAOYSA-N 6-(methoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridin-8-ol Chemical compound C1=C(COC)C=C(O)C2=NC(C)=C(C)N21 ICBCHJDVBWROGM-UHFFFAOYSA-N 0.000 description 2
- VOTVKOBZHSORGR-NVXWUHKLSA-N 8-[[(1r,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1OC1=CC(C(O)=O)=CN2C1=NC(C)=C2C VOTVKOBZHSORGR-NVXWUHKLSA-N 0.000 description 2
- XSJNIFBQXHFNIN-UHFFFAOYSA-N 8-hydroxy-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1=C(C(=O)N(C)C)C=C(O)C2=NC(C)=C(C)N21 XSJNIFBQXHFNIN-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 208000028774 intestinal disease Diseases 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PMBNZGLPCRRWTP-UHFFFAOYSA-N methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C(N)C2=NC(C)=C(C)N21 PMBNZGLPCRRWTP-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 208000018556 stomach disease Diseases 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- UKGCFMYYDATGNN-DTWKUNHWSA-N (1ar,6as)-6,6a-dihydro-1ah-indeno[1,2-b]oxirene Chemical compound C12=CC=CC=C2C[C@H]2[C@@H]1O2 UKGCFMYYDATGNN-DTWKUNHWSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ZWBOIOUXXAJRAU-UHFFFAOYSA-N 1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene Chemical compound C1CC2=CC=CC=C2C2C1O2 ZWBOIOUXXAJRAU-UHFFFAOYSA-N 0.000 description 1
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- KQFIATWLSFGEPF-UHFFFAOYSA-N 2,3-dimethylimidazo[1,2-a]pyridine Chemical compound C1=CC=CN2C(C)=C(C)N=C21 KQFIATWLSFGEPF-UHFFFAOYSA-N 0.000 description 1
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- OEZUGPONVBGGCQ-UHFFFAOYSA-N 2-methoxy-6,6a-dihydro-1ah-indeno[1,2-b]oxirene Chemical compound COC1=CC=CC2=C1C1OC1C2 OEZUGPONVBGGCQ-UHFFFAOYSA-N 0.000 description 1
- LYFVWFUZJCAEIO-UHFFFAOYSA-N 2-methyl-6,6a-dihydro-1ah-indeno[1,2-b]oxirene Chemical compound CC1=CC=CC2=C1C1OC1C2 LYFVWFUZJCAEIO-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- DYNNJEZMHOKBPQ-OVAHNPOGSA-N 8-[[(1r,2r)-2-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl]oxy]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide;hydrochloride Chemical compound Cl.C([C@H]1O)CC2=CC=CC=C2[C@H]1OC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 DYNNJEZMHOKBPQ-OVAHNPOGSA-N 0.000 description 1
- ABOUIPQLSAIXST-IAGOWNOFSA-N 8-[[(1r,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1NC1=CC(C(O)=O)=CN2C1=NC(C)=C2C ABOUIPQLSAIXST-IAGOWNOFSA-N 0.000 description 1
- AYRINRHOPXSPJR-QZTJIDSGSA-N 8-[[(1r,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-n,2,3-trimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1NC1=CC(C(=O)NC)=CN2C(C)=C(C)N=C21 AYRINRHOPXSPJR-QZTJIDSGSA-N 0.000 description 1
- CDTUMOAUIVWZCB-RTBURBONSA-N 8-[[(1r,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1NC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 CDTUMOAUIVWZCB-RTBURBONSA-N 0.000 description 1
- IGZWCZAEOZUVAM-XLIONFOSSA-N 8-[[(1r,2r)-2-hydroxy-7-methyl-2,3-dihydro-1h-inden-1-yl]oxy]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C([C@H]1O)C2=CC=CC(C)=C2[C@H]1OC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 IGZWCZAEOZUVAM-XLIONFOSSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YJQASIIPQFONQM-UHFFFAOYSA-N CC1=C(N2C=C(C=C(C2=N1)O)C(=O)O)C Chemical compound CC1=C(N2C=C(C=C(C2=N1)O)C(=O)O)C YJQASIIPQFONQM-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000258 cyclohexylethoxy group Chemical group [H]C([H])(O*)C([H])([H])C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- XFZLCTUONFKKGV-UHFFFAOYSA-N ethyl 2,3-dimethyl-8-phenylmethoxyimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C12=NC(C)=C(C)N2C=C(C(=O)OCC)C=C1OCC1=CC=CC=C1 XFZLCTUONFKKGV-UHFFFAOYSA-N 0.000 description 1
- XTIYKXYLASGUCR-UHFFFAOYSA-N ethyl 8-hydroxy-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C1=C(C(=O)OCC)C=C(O)C2=NC(C)=C(C)N21 XTIYKXYLASGUCR-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- VNYQRGMIGITTPB-QZTJIDSGSA-N methyl 8-[[(1r,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1NC1=CC(C(=O)OC)=CN2C(C)=C(C)N=C21 VNYQRGMIGITTPB-QZTJIDSGSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LWAMVUQSHUBRLK-UHFFFAOYSA-N n,n,2,3-tetramethyl-8-phenylmethoxyimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C12=NC(C)=C(C)N2C=C(C(=O)N(C)C)C=C1OCC1=CC=CC=C1 LWAMVUQSHUBRLK-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02025866 | 2002-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200503224B true ZA200503224B (en) | 2005-11-22 |
Family
ID=32319543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200503224A ZA200503224B (en) | 2002-11-19 | 2005-04-21 | 8-Substituted imidazopyridines. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7326718B2 (no) |
| EP (1) | EP1565465A1 (no) |
| JP (1) | JP2006508142A (no) |
| KR (1) | KR20050086584A (no) |
| CN (1) | CN100384842C (no) |
| AU (1) | AU2003288071A1 (no) |
| BR (1) | BR0316201A (no) |
| CA (1) | CA2506027A1 (no) |
| EA (1) | EA008304B1 (no) |
| HR (1) | HRP20050528A2 (no) |
| MX (1) | MXPA05005117A (no) |
| NO (1) | NO20052857L (no) |
| NZ (1) | NZ540504A (no) |
| PL (1) | PL375567A1 (no) |
| RS (1) | RS20050377A (no) |
| WO (1) | WO2004046144A1 (no) |
| ZA (1) | ZA200503224B (no) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102152809B1 (ko) * | 2004-07-28 | 2020-09-07 | 다케다 야쿠힌 고교 가부시키가이샤 | 피롤로〔2,3-ｃ〕피리딘 화합물, 그 제조 방법 및 용도 |
| KR20070086294A (ko) * | 2004-12-17 | 2007-08-27 | 화이자 인코포레이티드 | 산 펌프 길항물질로 유용한 크로만 유도체 |
| TW200700064A (en) * | 2005-03-24 | 2007-01-01 | Glaxo Group Ltd | Novel compounds |
| GB0513423D0 (en) * | 2005-06-30 | 2005-08-03 | Glaxo Group Ltd | Novel compounds |
| WO2007026218A2 (en) * | 2005-09-01 | 2007-03-08 | Pfizer Japan Inc. | Chromane substituted 2-alkyl imidazopyridine derivatives and use thereof as acid pump antagonists |
| EP1934215A1 (en) * | 2005-09-22 | 2008-06-25 | Nycomed GmbH | Isotopically substituted imidazopyridine derivatives for the treatment of gastrointestinal disorders |
| BRPI0708808A2 (pt) * | 2006-03-17 | 2011-06-14 | Raqualia Pharma Inc | Derivados de cromano |
| WO2008071766A2 (en) * | 2006-12-14 | 2008-06-19 | Nycomed Gmbh | Spiro-indene substituted imidazonaphythyridine and pyranoimidazopyridine derivatives as inhibitors of gastric acid secretion |
| EP2452680B1 (en) | 2009-07-09 | 2019-12-18 | RaQualia Pharma Inc. | Acid pump antagonist for the treatment of diseases involved in abnormal gastrointestinal motility |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL86269A0 (en) * | 1987-05-08 | 1988-11-15 | Byk Gulden Lomberg Chem Fab | Imidazole derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5112834A (en) * | 1987-07-16 | 1992-05-12 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Imidazole protectorant for the stomach and intestine |
| EP0368158A1 (de) * | 1988-11-07 | 1990-05-16 | Byk Gulden Lomberg Chemische Fabrik GmbH | Neue Imidazopyridine |
| DE69823493T2 (de) * | 1997-03-24 | 2009-09-24 | Nycomed Gmbh | Tetrahydropyridoverbindungen |
| CN101255164A (zh) | 1997-05-28 | 2008-09-03 | 奥坦纳医药公司 | 稠合的二氢吡喃类化合物及其用途 |
| HUP0001555A3 (en) | 1997-10-30 | 2001-01-29 | Altana Pharma Ag | Tetrahydro-imidazo-naphthyridine derivatives, pharmaceutical compositions thereof and process for their preparation |
| SE9801526D0 (sv) | 1998-04-29 | 1998-04-29 | Astra Ab | New compounds |
| EE04677B1 (et) | 1998-09-23 | 2006-08-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahdropridoeetrid, nende kasutamine ja ravim |
| ATE386742T1 (de) | 1998-11-03 | 2008-03-15 | Nycomed Gmbh | Imidazonaphthyridine |
| AU3966600A (en) | 1999-04-17 | 2000-11-02 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Haloalkoxy imidazonaphthyridines |
| MXPA02009549A (es) | 2000-03-29 | 2004-05-14 | Altana Pharma Ag | Imidazopiridinas triciclicas. |
| IL151201A0 (en) | 2000-03-29 | 2003-04-10 | Altana Pharma Ag | Alkylated imidazopyridine derivatives and pharmaceutical compositions containing the same |
| ES2298233T3 (es) | 2000-03-29 | 2008-05-16 | Nycomed Gmbh | Derivados de pirano(2,3-c)imidazo(1,2-a)piridina para el tratamiento de trastornos gastrointestinales. |
| ES2253376T3 (es) | 2000-03-29 | 2006-06-01 | Altana Pharma Ag | Profarmacos de derivados de imidazopiridina. |
| SE0100297D0 (sv) | 2001-02-01 | 2001-02-01 | Astrazeneca Ab | New compounds |
| SE0100295D0 (sv) | 2001-02-01 | 2001-02-01 | Astrazeneca Ab | New compounds |
| SE0100296D0 (sv) | 2001-02-01 | 2001-02-01 | Astrazeneca Ab | New compounds |
-
2003
- 2003-11-15 MX MXPA05005117A patent/MXPA05005117A/es not_active Application Discontinuation
- 2003-11-15 KR KR1020057008530A patent/KR20050086584A/ko not_active Application Discontinuation
- 2003-11-15 JP JP2004552614A patent/JP2006508142A/ja not_active Withdrawn
- 2003-11-15 PL PL03375567A patent/PL375567A1/xx not_active Application Discontinuation
- 2003-11-15 AU AU2003288071A patent/AU2003288071A1/en not_active Abandoned
- 2003-11-15 EA EA200500711A patent/EA008304B1/ru not_active IP Right Cessation
- 2003-11-15 CA CA002506027A patent/CA2506027A1/en not_active Abandoned
- 2003-11-15 NZ NZ540504A patent/NZ540504A/en unknown
- 2003-11-15 EP EP03779937A patent/EP1565465A1/en not_active Withdrawn
- 2003-11-15 WO PCT/EP2003/012787 patent/WO2004046144A1/en active Application Filing
- 2003-11-15 CN CNB2003801025858A patent/CN100384842C/zh not_active Expired - Fee Related
- 2003-11-15 US US10/534,741 patent/US7326718B2/en not_active Expired - Fee Related
- 2003-11-15 BR BR0316201-0A patent/BR0316201A/pt not_active IP Right Cessation
- 2003-11-15 RS YUP-2005/0377A patent/RS20050377A/sr unknown
-
2005
- 2005-04-21 ZA ZA200503224A patent/ZA200503224B/en unknown
- 2005-06-10 HR HR20050528A patent/HRP20050528A2/xx not_active Application Discontinuation
- 2005-06-13 NO NO20052857A patent/NO20052857L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004046144A8 (en) | 2007-03-22 |
| AU2003288071A1 (en) | 2004-06-15 |
| HRP20050528A2 (en) | 2006-06-30 |
| EP1565465A1 (en) | 2005-08-24 |
| CN1708497A (zh) | 2005-12-14 |
| EA008304B1 (ru) | 2007-04-27 |
| WO2004046144A1 (en) | 2004-06-03 |
| PL375567A1 (en) | 2005-11-28 |
| BR0316201A (pt) | 2005-10-04 |
| JP2006508142A (ja) | 2006-03-09 |
| EA200500711A1 (ru) | 2005-12-29 |
| CA2506027A1 (en) | 2004-06-03 |
| US7326718B2 (en) | 2008-02-05 |
| US20060100234A1 (en) | 2006-05-11 |
| RS20050377A (en) | 2007-11-15 |
| NZ540504A (en) | 2007-12-21 |
| NO20052857L (no) | 2005-06-13 |
| CN100384842C (zh) | 2008-04-30 |
| KR20050086584A (ko) | 2005-08-30 |
| MXPA05005117A (es) | 2005-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200503224B (en) | 8-Substituted imidazopyridines. | |
| MX2007011238A (es) | Metodo para la fabricacion de 1h-imidazo[4,5-c]quinolin-4-aminas 1-sustituidas y sus intermedios. | |
| JP2008540628A (ja) | ファムシクロビルおよび他のプリン誘導体の調製 | |
| ZA200407766B (en) | Novel alkoxypyridine-derivatives | |
| EP1313740B1 (en) | Prodrugs of imidazopyridine derivatives | |
| AU4422501A (en) | Alkylated imidazopyridine derivatives | |
| WO2009125425A2 (en) | Improved process for the preparation of (s.s)-2.8-diazabicyclo[4.3.0]nonane | |
| JP5635418B2 (ja) | 鏡像異性的に純粋なインドロピリジンの調製方法 | |
| EP1917263B1 (en) | Process for the preparation of imidazopyridines | |
| EP1758900B1 (en) | Substituted tricyclic benzimidazoles | |
| EP1824850A2 (en) | SUBSTITUTED IMIDAZO[4,5-b]PYRIDINES AS INHIBITORS OF GASTRIC ACID SECRETION | |
| AU2007228939A1 (en) | Process for preparing l-halo-2,7-naphthyridinyl derivatives | |
| AU783550B2 (en) | Imidazopyridin-8-ones | |
| EP1631571B1 (en) | Novel intermediate for the preparation of therapeutically active imidazopyridines | |
| EP3911649A1 (en) | A process for the preparation of tetrahydropyridopyrimidines | |
| JP2005500372A (ja) | 三環エポキシド | |
| AU2004235981A1 (en) | Imidazopyridine intermediates | |
| AU2005212855A1 (en) | Tricyclic imidazopyridines and intermediates for the synthesis thereof | |
| ZA200503910B (en) | 4-substituted benzimidazoles and their use as inhibitors of gastric secretion |